Patent NZ-500958-A (NZ)
Title: 6-substituted 1,2,4a,5a,8a,8b-hexahydro- and 1,2,3,4,4a,5a,8a,8b-octahydro-6H-pyrrolo [3',4':4,5]furo[3,2-b]pyrid-8(7H)-on derivatives and their use in combatting endoparasites
Inventor: JESCHKE PETER
IPC: C07D491/14
Filed: 1998-04-29
Abstract: 6-substituted 1,2,4a,5a,8a,8b-hexahydro- and 1,2,3,4,4a,5a,8a,8b-octahydro-6H-pyrrolo[3',4':4,5]furo[3,2-b]pyrid-8 7H -one derivatives of general formula (I) and their salts, in which: R1 is hydrogen or optionally substituted alkyl, cycloalkyl, arylalkyl, aryl, heteroaryl or herarylalkyl; R2 is hydrogen or optionally substituted alkyl, cycloalkyl or alkoxycarbonyl; Or R1 and R2 together with the atoms to which they are attached represent an optionally substituted 5- or 6-membered ring, which may be optionally interrupted by oxygen, sulphur, sulphoxyl or sulphonyl; R3 represents hydrogen or optionally substituted alkyl, cycloalkyl or alkoxycarbonyl; R4 represents hydrogen or optionally substituted alkyl, alkenyl, alkinyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, heraryl, hetarylalkyl, amino, alkylamino, di-alkylamino or cycloalkylamino; A represents hydroxy, alkoxy, alkenyloxy, alkinyloxy, arylalkyloxy, formyloxy, azido, halogen, aryloxy, hetarylalkyloxy, hetaryloxy, mercapto, alkylthio, alkylsulphonyl, alkenylthio, arylalkylsulphonyl, hetarylalkylthio, hetarylalkylsulphonyl, arylthio, arylsulphonyl, alkyl, alkenyl, alkinyl, aryl, arylalkyl, hetaryl, hetarylalkyl, alkoxycarbonyl, -X-G(=Y)-Q, CHR6=C(=O)-R7 OR, -O-B1; X represents oxygen or sulphur; -G(=Y)- represents carbonyl, thiocarbonyl, sulphoxyl, sulphonyl, -P(O)-O-R5 OR -P(S)-O-R5; Q represents alkyl, alkenyl, alkinyl, cycloalkyl, alkoxy, alkenyloxy, alkinyloxy, aryl arylalkyl, cycloalkyoxy, hetaryl, hetarylalkyl, an optionally substituted cyclic amino group which is attached via the nitrogen atom; R5 represents alkyl; R6 represents hydrogen alkyl, alkoxy, arylalkoxy, alkylthio, cycloalkylthio, arylthio, hetarylaIkylthio; R7 represents optionally substituted alkyl, alkenyl, cycloalkyl, alkylthio, arylthio, aryl, arylalkyl, hetaryl or hetarylalkyl; Or R6 and R 7 together with the atoms to which they are attached represent a 5-, 6- or 7-membered carbocyclic ring, which may optionally be substituted, B represents hydrogen or optionally substituted alkyl, alkenyl, alkinyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, hetaryl, hetarylalkyl, formyl, alkoxydicarbonyl or a radical from the group consisting of B I, B2, B3 and B4 R8 represents hydrogen or optionally substituted, alkyl, cycloalkyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl; R8 and R9 together with the atoms to which they are attached represent an optionally substituted 5- or 6-membered ring, which is optionally interrupted by oxygen, sulphur, sulphoxyl or sulphonyl; R9 and R10 each represent hydrogen, alkyl, alkenyl, cycloalkyl or optionally substituted aryl, arylalkyl, hetaryl or hetarylalkyl; Or R9 and R10 together represent an optionally substituted spirocyclic ring;  -G1(=Y1)- represents carboxyl, thiocarboxyl, -C=CH-NO2, -C=CH-CN, -C=N-R11, sulphoxyl, sulphonyl, -P(O)-O-R5 or -P(S)-O-R5, R11 represents hydrogen, hydroxyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, halogenoalkylcarbonyl, alkylsulphonyl, nitro or cyano; Q represents optionally substituted alkyl, alkenyl, alkinyl, cycloalkyl, aryl, arylalkyl, hetaryl or hetarylalkyl, or a radical selected from the group consisting of G1 and G2; -G2(=Y2)- may represent carboxyl, thiocarboxyl or sulphonyl; Z represents oxygen, sulphur or -NR13; R12 may, if Z is nitrogen, represent a cyclic amino group, which is attached via a nitrogen atom; R12 and R13 independently of one another represent hydrogen or optionally substituted alkyl, alkenyl, alkinyl, cycloalkyl, cycloalkylalkyl, alkoxycarbonyl, aryl, arylalkyl, hetaryl or hetarylalkyl; R12 and R13 together with the adjacent N atom represent an optionally substituted carbocyclic 5-, 6- or 7-membered ring system or represent a 7- to 10-membered bicyclic ring system, which may optionally be interrupted by oxygen, sulphur, sulphoxyl, sulphonyl, carbonyl, -N-O, -N=, -NR15- or by quarternized nitrogen; R14 represents hydrogen or alkyl; R15 represents hydrogen or optionally substituted alkyl, alkenyl, alkinyl, cycloalkyl, cycloalkylalkyl, alkoxycar, alkylcarbonyl, cycloalkylcarbonyl, cyano, aryl, arylalkyl, hetaryl, hetarylalkyl; The dotted line is absent or represents a single bond. The compounds are useful in combatting endoparasites.